JP2006507241A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006507241A5 JP2006507241A5 JP2004529002A JP2004529002A JP2006507241A5 JP 2006507241 A5 JP2006507241 A5 JP 2006507241A5 JP 2004529002 A JP2004529002 A JP 2004529002A JP 2004529002 A JP2004529002 A JP 2004529002A JP 2006507241 A5 JP2006507241 A5 JP 2006507241A5
- Authority
- JP
- Japan
- Prior art keywords
- methanone
- diazabicyclo
- furan
- thiophen
- pyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- -1 1,4-diazabicyclo [3.2.2] non-4-yl Chemical group 0.000 claims 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 4
- GNPQLYUSJOCBMA-UHFFFAOYSA-N (5-bromofuran-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound O1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 GNPQLYUSJOCBMA-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 230000006735 deficit Effects 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- OGZLAVDBQCWTRH-UHFFFAOYSA-N (3-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 OGZLAVDBQCWTRH-UHFFFAOYSA-N 0.000 claims 1
- CSIFTQTVMGTFIA-UHFFFAOYSA-N (4-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 CSIFTQTVMGTFIA-UHFFFAOYSA-N 0.000 claims 1
- PFARLMJTRBXTQP-UHFFFAOYSA-N (4-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CSC(C(=O)N2C3CCN(CC3)CC2)=C1 PFARLMJTRBXTQP-UHFFFAOYSA-N 0.000 claims 1
- PFOHKMLFVACSFW-UHFFFAOYSA-N (5-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 PFOHKMLFVACSFW-UHFFFAOYSA-N 0.000 claims 1
- DNQWTTQUOXMVJD-UHFFFAOYSA-N (5-bromothiophen-3-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC(C(=O)N2C3CCN(CC3)CC2)=C1 DNQWTTQUOXMVJD-UHFFFAOYSA-N 0.000 claims 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 1
- UVZLCLJQMZJFJL-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-iodophenyl)methanone Chemical compound IC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 UVZLCLJQMZJFJL-UHFFFAOYSA-N 0.000 claims 1
- IXKRDKNQHUOVKG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 IXKRDKNQHUOVKG-UHFFFAOYSA-N 0.000 claims 1
- UCMQCNNZHLFWQP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=N1 UCMQCNNZHLFWQP-UHFFFAOYSA-N 0.000 claims 1
- CDSCDKTXQWLABR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CN=C1 CDSCDKTXQWLABR-UHFFFAOYSA-N 0.000 claims 1
- GENNWRVZHQPVBO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=NC=C1 GENNWRVZHQPVBO-UHFFFAOYSA-N 0.000 claims 1
- LFQXLDRICKOWGM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CS1 LFQXLDRICKOWGM-UHFFFAOYSA-N 0.000 claims 1
- FUDFPUYWRXFOOH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C=1C=CSC=1 FUDFPUYWRXFOOH-UHFFFAOYSA-N 0.000 claims 1
- HAXPXNGBJPFDGV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)N1C(CC2)CCN2CC1 HAXPXNGBJPFDGV-UHFFFAOYSA-N 0.000 claims 1
- WTSKNUGIAJZTMU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WTSKNUGIAJZTMU-UHFFFAOYSA-N 0.000 claims 1
- YFNUMKDCWUSIRV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=C1 YFNUMKDCWUSIRV-UHFFFAOYSA-N 0.000 claims 1
- MZMRVHKSQCNPKT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CC=N1 MZMRVHKSQCNPKT-UHFFFAOYSA-N 0.000 claims 1
- RJJNRYMNCLCVOG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=N1 RJJNRYMNCLCVOG-UHFFFAOYSA-N 0.000 claims 1
- ZNVCOLOEINQRSA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=N1 ZNVCOLOEINQRSA-UHFFFAOYSA-N 0.000 claims 1
- QOXDDTRJHUWFSC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CN=C1 QOXDDTRJHUWFSC-UHFFFAOYSA-N 0.000 claims 1
- DHJJHUMTVYKNTK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 DHJJHUMTVYKNTK-UHFFFAOYSA-N 0.000 claims 1
- MYRASTOHFZHWRQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CN=C1 MYRASTOHFZHWRQ-UHFFFAOYSA-N 0.000 claims 1
- IDJXUTJMHGLAQD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=NC=C1 IDJXUTJMHGLAQD-UHFFFAOYSA-N 0.000 claims 1
- IRIRSSBNMMWXKV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=NC=C1 IRIRSSBNMMWXKV-UHFFFAOYSA-N 0.000 claims 1
- SFCOAMGARZGOFF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=NC=C1 SFCOAMGARZGOFF-UHFFFAOYSA-N 0.000 claims 1
- PNHMVUPZQHFWJP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CS1 PNHMVUPZQHFWJP-UHFFFAOYSA-N 0.000 claims 1
- IQQWZDQMXJJYNM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CS1 IQQWZDQMXJJYNM-UHFFFAOYSA-N 0.000 claims 1
- JTOZWWPPPIVSJG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CS1 JTOZWWPPPIVSJG-UHFFFAOYSA-N 0.000 claims 1
- HSLQOYKHBCLWOB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C=1C=CSC=1 HSLQOYKHBCLWOB-UHFFFAOYSA-N 0.000 claims 1
- SODJXZKVCLJFEE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=C1 SODJXZKVCLJFEE-UHFFFAOYSA-N 0.000 claims 1
- LHGVLQATESRNBH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CC=C1 LHGVLQATESRNBH-UHFFFAOYSA-N 0.000 claims 1
- DXAUAUZCOKVAJC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CC=N1 DXAUAUZCOKVAJC-UHFFFAOYSA-N 0.000 claims 1
- DLHCGZZYPGPVCR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CC=N1 DLHCGZZYPGPVCR-UHFFFAOYSA-N 0.000 claims 1
- MVCSWWMDCPXUOW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=N1 MVCSWWMDCPXUOW-UHFFFAOYSA-N 0.000 claims 1
- QPPBIBLFYOSNPS-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CC=N1 QPPBIBLFYOSNPS-UHFFFAOYSA-N 0.000 claims 1
- MRQVRJKCJRBPAD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CN=C1 MRQVRJKCJRBPAD-UHFFFAOYSA-N 0.000 claims 1
- MBWNIKDPLGYNBF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CN=C1 MBWNIKDPLGYNBF-UHFFFAOYSA-N 0.000 claims 1
- ZXSSSLLUZQKGDV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CN=C1 ZXSSSLLUZQKGDV-UHFFFAOYSA-N 0.000 claims 1
- MKBBUDXINIFDPX-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CN=C1 MKBBUDXINIFDPX-UHFFFAOYSA-N 0.000 claims 1
- MWXBVPSLVKVWBA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=NC=C1 MWXBVPSLVKVWBA-UHFFFAOYSA-N 0.000 claims 1
- MBEIHBWZBVTMFZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=NC=C1 MBEIHBWZBVTMFZ-UHFFFAOYSA-N 0.000 claims 1
- KEJSEMWXIQEIDY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=NC=C1 KEJSEMWXIQEIDY-UHFFFAOYSA-N 0.000 claims 1
- RLJRNTDELRCHII-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=NC=C1 RLJRNTDELRCHII-UHFFFAOYSA-N 0.000 claims 1
- CFSYVLPMJBCKBT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CS1 CFSYVLPMJBCKBT-UHFFFAOYSA-N 0.000 claims 1
- HYMMMRPPFFEINN-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CS1 HYMMMRPPFFEINN-UHFFFAOYSA-N 0.000 claims 1
- CLBALKICHJMDDY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CS1 CLBALKICHJMDDY-UHFFFAOYSA-N 0.000 claims 1
- FTMRKAUMDVXFDC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CS1 FTMRKAUMDVXFDC-UHFFFAOYSA-N 0.000 claims 1
- ADRZDHXTXVMBOR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C=1C=CSC=1 ADRZDHXTXVMBOR-UHFFFAOYSA-N 0.000 claims 1
- AJJFWAVQFNELFJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C=1C=CSC=1 AJJFWAVQFNELFJ-UHFFFAOYSA-N 0.000 claims 1
- JYSBTOLWQZATNJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C=1C=CSC=1 JYSBTOLWQZATNJ-UHFFFAOYSA-N 0.000 claims 1
- YYSWQOGFUOIEAW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C=1C=CSC=1 YYSWQOGFUOIEAW-UHFFFAOYSA-N 0.000 claims 1
- UYXQTYKMPHONOO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[3-(furan-2-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CO1 UYXQTYKMPHONOO-UHFFFAOYSA-N 0.000 claims 1
- DLASHEKCTDFEAZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[3-(furan-3-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C=1C=COC=1 DLASHEKCTDFEAZ-UHFFFAOYSA-N 0.000 claims 1
- ZZMOMAZUUAPGBY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CO1 ZZMOMAZUUAPGBY-UHFFFAOYSA-N 0.000 claims 1
- DHQSIENQTWLGCD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CO1 DHQSIENQTWLGCD-UHFFFAOYSA-N 0.000 claims 1
- CEHAHHKXNFJLFU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CO1 CEHAHHKXNFJLFU-UHFFFAOYSA-N 0.000 claims 1
- AUDBITKNIDHJPP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-3-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C=1C=COC=1 AUDBITKNIDHJPP-UHFFFAOYSA-N 0.000 claims 1
- CVFFPZUTOZEQBY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-3-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C=1C=COC=1 CVFFPZUTOZEQBY-UHFFFAOYSA-N 0.000 claims 1
- ZOADDVPJZZWKDO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-3-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C=1C=COC=1 ZOADDVPJZZWKDO-UHFFFAOYSA-N 0.000 claims 1
- BIAAPEZXONIEPI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-2-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CO1 BIAAPEZXONIEPI-UHFFFAOYSA-N 0.000 claims 1
- CHLWYKCXPSNISN-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-2-yl)furan-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CO1 CHLWYKCXPSNISN-UHFFFAOYSA-N 0.000 claims 1
- SNKRQFHZWIGOEW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-2-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CO1 SNKRQFHZWIGOEW-UHFFFAOYSA-N 0.000 claims 1
- VBGJVKGJWKENNB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-2-yl)thiophen-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CO1 VBGJVKGJWKENNB-UHFFFAOYSA-N 0.000 claims 1
- GZLLLTUIOLORTQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C=1C=COC=1 GZLLLTUIOLORTQ-UHFFFAOYSA-N 0.000 claims 1
- CQFWWHVPHZLRIX-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)furan-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C=1C=COC=1 CQFWWHVPHZLRIX-UHFFFAOYSA-N 0.000 claims 1
- MIJYHLLUFJGZPR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C=1C=COC=1 MIJYHLLUFJGZPR-UHFFFAOYSA-N 0.000 claims 1
- KPDXQGPZVDOPAC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)thiophen-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C=1C=COC=1 KPDXQGPZVDOPAC-UHFFFAOYSA-N 0.000 claims 1
- PIXDIVGXUUHIPV-UHFFFAOYSA-N 4-thiophen-3-ylthiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(C2=CSC=C2)=C1 PIXDIVGXUUHIPV-UHFFFAOYSA-N 0.000 claims 1
- WJTFHWXMITZNHS-UHFFFAOYSA-N 5-bromofuran-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)O1 WJTFHWXMITZNHS-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000003935 attention Effects 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 claims 1
- 230000007278 cognition impairment Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 210000000225 synapse Anatomy 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0202430A SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | New Compounds |
| PCT/SE2003/001277 WO2004016617A1 (en) | 2002-08-14 | 2003-08-13 | Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006507241A JP2006507241A (ja) | 2006-03-02 |
| JP2006507241A5 true JP2006507241A5 (enrdf_load_stackoverflow) | 2006-09-14 |
Family
ID=20288725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004529002A Pending JP2006507241A (ja) | 2002-08-14 | 2003-08-13 | ニコチン性アセチルコリン作用剤としてのビアリールジアザビシクロアルカンアミド |
Country Status (18)
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| BR0314485A (pt) | 2002-09-25 | 2005-07-26 | Memory Pharm Corp | Indazóis, benzotiazóis e benzoisotiazóis, composto, composição farmacêutica, método desativação/estimulação seletiva de receptores nicotìnicos de a-7 em um mamìfero e método de tratamento e/ou prevenção de uma doença com os mesmos |
| EP1803444B2 (en) | 2002-12-20 | 2025-08-06 | NicoNovum AB | A method for the preparation of a nicotine-containing particulate material with a crystalline cellulose (in particular MCC) |
| DE602004023586D1 (de) * | 2003-02-27 | 2009-11-26 | Neurosearch As | Neue diazabicyclische arylderivate |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| PT1697378E (pt) | 2003-12-22 | 2008-02-28 | Memory Pharm Corp | Indoles, 1h-indazoles, 1,2-benzisoxazoles e 1,2-benzisotiazoles, sua preparação e utilizações |
| CN100445285C (zh) * | 2003-12-22 | 2008-12-24 | 阿斯利康(瑞典)有限公司 | 烟碱性乙酰胆碱受体配体 |
| WO2005075482A1 (en) * | 2004-02-04 | 2005-08-18 | Neurosearch A/S | Diazabicyclic aryl derivatives as nicotinic acetylcholine receptor ligands |
| KR101176670B1 (ko) | 2004-03-25 | 2012-08-23 | 메모리 파마슈티칼스 코포레이션 | 인다졸, 벤조티아졸, 벤조이소티아졸, 벤즈이속사졸, 및그의 제조법 및 용도 |
| EP1742944B1 (en) | 2004-04-22 | 2010-11-10 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| DE602005027452D1 (de) | 2004-05-07 | 2011-05-26 | Memory Pharm Corp | 1h-indazole, benzothiazole, 1,2-benzisoxazole, 1,2-benzisothiazole und chromone und deren herstellung und verwendungen |
| CN100588657C (zh) * | 2004-10-15 | 2010-02-10 | 神经研究公司 | 新的氮杂双环芳基衍生物及其医药用途 |
| CN101124224A (zh) | 2004-12-22 | 2008-02-13 | 记忆药物公司 | 烟碱性α-7受体配体及其制备和用途 |
| JP2009526777A (ja) | 2006-02-14 | 2009-07-23 | ノイロサーチ アクティーゼルスカブ | ニコチン性アセチルコリン受容体作用薬としての３，９−ジアザビシクロ（３．３．１）ノナ−３−イル−アリールメタノン誘導体 |
| CA2646942C (en) | 2006-03-16 | 2014-07-29 | Niconovum Ab | Improved snuff composition |
| AU2007267176A1 (en) | 2006-05-30 | 2007-12-06 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidinyl derivatives and their medical use |
| TWI404532B (zh) * | 2006-11-02 | 2013-08-11 | Targacept Inc | 菸鹼乙醯膽鹼受體亞型選擇性之二氮雜雙環烷類醯胺 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| KR20100087172A (ko) * | 2007-10-22 | 2010-08-03 | 메모리 파마슈티칼스 코포레이션 | 질환의 치료에 유용한, 니코틴성 아세틸콜린 수용체에 대한 (１,４-디아자-바이시클로[３.２.２]논-６-엔-４-일)-헤테로시클릴-메타논 리간드 |
| GB0724251D0 (en) | 2007-12-12 | 2008-02-06 | Univ Edinburgh | Therapeutic compounds and their use |
| GB0804685D0 (en) | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| BRPI0914231A2 (pt) | 2008-06-20 | 2015-11-03 | Atrazeneca Ab | composto, composição farmacêutica, método para tratar um distúrbio psiquiátrico, e, uso de um composto |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| EP2443113A1 (en) | 2009-06-15 | 2012-04-25 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| CA2772504C (en) | 2009-09-16 | 2017-10-24 | The University Of Edinburgh | (4-phenyl-piperidin-1-yl)-[5-(1h-pyrazol-4-yl)-thiophen-3-yl]-methanone compounds and their use |
| US9199914B2 (en) | 2010-02-03 | 2015-12-01 | Meh Associates, Inc. | Multiple substituted fluoromethanes as selective and bioactive isosteres |
| EP2563780B1 (en) | 2010-04-29 | 2015-05-06 | The University Of Edinburgh | 3,3-disubstituted-(8-aza-bicyclo[3.2.1]oct-8-yl)-[5-(1h-pyrazol-4-yl)-thiophen-3-yl]-methanones as inhibitors of 11(beta)-hsd1 |
| SA111320455B1 (ar) | 2010-05-17 | 2014-10-16 | Envivo Pharmaceuticals Inc | صورة بلورية من (R)-7- كلورو -N- (كينوكليدين -3- يل) بنزو[b] ثيوفين -2- كربوكساميد هيدروكلوريد أحادي الهيدرات |
| WO2012007500A2 (de) * | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| AU2013259871A1 (en) | 2012-05-08 | 2014-11-20 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| WO2014122474A1 (en) | 2013-02-07 | 2014-08-14 | Takeda Pharmaceutical Company Limited | Piperidin-1 -yl and azepin-1 -yl carboxylates as muscarinic m4 receptor agonists |
| CN105324372B (zh) | 2013-06-21 | 2018-03-06 | 武田药品工业株式会社 | 作为前动力蛋白受体调节剂的1‑磺酰基哌啶衍生物 |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| WO2021156769A1 (en) | 2020-02-03 | 2021-08-12 | Genzyme Corporation | Methods for treating neurological symptoms associated with lysosomal storage diseases |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
| JP2023534322A (ja) | 2020-07-24 | 2023-08-09 | ジェンザイム・コーポレーション | ベングルスタットを含む医薬組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281423A (en) * | 1964-02-03 | 1966-10-25 | Merck & Co Inc | 1, 3-ethanopiperazines and process |
| US4895943A (en) * | 1988-10-25 | 1990-01-23 | Pfizer Inc. | Preparation of 1,4-diazabicyclo(3.2.2)nonane |
| US5679673A (en) * | 1992-09-24 | 1997-10-21 | The United States Of America, Represented By The Department Of Health And Human Services | Aralkyl bridged diazabicycloalkane derivatives for CNS disorders |
| FR2791678B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, leur preparation et leur application en therapeutique |
| FR2809731B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| FR2809732B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| DE602004023586D1 (de) * | 2003-02-27 | 2009-11-26 | Neurosearch As | Neue diazabicyclische arylderivate |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| CN100445285C (zh) * | 2003-12-22 | 2008-12-24 | 阿斯利康(瑞典)有限公司 | 烟碱性乙酰胆碱受体配体 |
-
2002
- 2002-08-14 SE SE0202430A patent/SE0202430D0/xx unknown
-
2003
- 2003-08-13 US US10/524,484 patent/US20050239774A1/en not_active Abandoned
- 2003-08-13 AT AT03788214T patent/ATE417049T1/de not_active IP Right Cessation
- 2003-08-13 NZ NZ537882A patent/NZ537882A/en unknown
- 2003-08-13 EP EP03788214A patent/EP1539765B1/en not_active Expired - Lifetime
- 2003-08-13 DE DE60325234T patent/DE60325234D1/de not_active Expired - Fee Related
- 2003-08-13 ES ES03788214T patent/ES2316848T3/es not_active Expired - Lifetime
- 2003-08-13 MX MXPA05001583A patent/MXPA05001583A/es unknown
- 2003-08-13 KR KR1020057002265A patent/KR20060002727A/ko not_active Ceased
- 2003-08-13 WO PCT/SE2003/001277 patent/WO2004016617A1/en active Application Filing
- 2003-08-13 CN CNB038194791A patent/CN100343256C/zh not_active Expired - Fee Related
- 2003-08-13 JP JP2004529002A patent/JP2006507241A/ja active Pending
- 2003-08-13 BR BR0313234-0A patent/BR0313234A/pt not_active IP Right Cessation
- 2003-08-13 AU AU2003248592A patent/AU2003248592B2/en not_active Expired - Fee Related
- 2003-08-13 CA CA002493920A patent/CA2493920A1/en not_active Abandoned
-
2005
- 2005-01-20 IL IL16641605A patent/IL166416A0/xx unknown
- 2005-02-10 ZA ZA200501226A patent/ZA200501226B/en unknown
- 2005-03-11 NO NO20051259A patent/NO20051259L/no not_active Application Discontinuation